Tetrahydrofuran → 4-Bromo-1-fluoronaphthalene-2-carbaldehyde

A solution of 2,2,6,6-tetramethylpiperidine (4.13 ml) in tetrahydrofuran (40 ml) was cooled to −78° C. under argon atmosphere, and added dropwise thereto was n-butyl lithium (2.44 M hexane solution, 10.0 ml). The mixture was stirred at the same temperature for 30 minutes, and added dropwise thereto at −78° C. was a solution of 1-bromo-4-fluoronaphthalene (5.0 g) in tetrahydrofuran (20 ml). The mixture was stirred at the same temperature for 1 hour, and added dropwise thereto at −78° C. was N,N-dimethylformamide (5.16 ml). The mixture was stirred at the same temperature for 1 hour, and added thereto was a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from diisopropyl ether and hexane to give 4-bromo-1-fluoro-2-naphthaldehyde (4.43 g) as pale yellow crystals. APCI-Mass m/Z 267/269 (M+NH4).

1. additionadded dropwise
2. additionadded dropwise
3. customat −78° C.
4. stirringThe mixture was stirred at the same temperature for 1 hour
5. additionadded dropwise
6. customat −78° C.
7. stirringThe mixture was stirred at the same temperature for 1 hour
8. additionadded
9. extractionthe mixture was extracted with ethyl acetate
10. washThe extract was washed with water
11. dry with materialdried over magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was crystallized from diisopropyl ether and hexane

ORD record

ord-b7e70c61ec9e478a899330b2a6fe79c8

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2